Regioselective <em>O</em>-Glycosylation of Nucleosides <em>via</em> the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides

Hidehisa Someya; Taiki Itoh; Mebae Kato; Shin Aoki

doi:10.3791/57897

JoVE Journal > Chemistry

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Kimya

Regioselettiva O- glicosilazione dei nucleosidi tramite il temporaneo 2', 3'-diolo protezione da boronico per la sintesi di disaccaride nucleosidi

Published: July 26, 2018

doi:

10.3791/57897

Hidehisa Someya¹, Taiki Itoh¹, Mebae Kato¹, Shin Aoki^1,2

¹Farmasötik Bilimler Fakültesi,Tokyo University of Science, ²Imaging Frontier Center,Tokyo University of Science

Özet

Qui, presentiamo i protocolli per la sintesi dei nucleosidi disaccaride di regioselettiva O– glicosilazione di ribonucleosides tramite una protezione temporanea della loro 2′, 3′-diolo moiety utilizzando un estere boronico ciclico. Questo metodo si applica a diversi nucleosidi non protetti quali adenosina, guanosina, citidina, uridina, 5-methyluridine e 5-fluorouridine dare corrispondente nucleosidi disaccaride.

Abstract

Nucleosidi disaccaride, che consistono di disaccaride e nucleobase moiety, sono stati conosciuti come un prezioso gruppo di prodotti naturali, avendo molteplici bioattività. Anche se chimica O– glycosylation è una strategia comunemente benefica per sintetizzare nucleosidi disaccaride, la preparazione di substrati come glicosil donatori e accettori richiede protezione gruppo noioso manipolazioni e una purificazione presso ogni passo sintetico. Nel frattempo, diversi gruppi di ricerca hanno riferito che boronico ed esteri di Borinici servono come una protezione o attivazione di un gruppo di derivati di carboidrati per ottenere il regio – e/o stereoselettiva acilazione, alchilazione, sililazione e glicosilazione. In questo articolo, dimostriamo la procedura per la regioselettiva O– glicosilazione di ribonucleosides non protetti utilizzando acido boronico. L’esterificazione di 2′, 3′-diolo di ribonucleosides con Acido boronico rende la protezione temporanea di diolo e, O– glycosylation seguente con un glicosil donatore in presenza di p– toluenesulfenyl cloruro e argento TRIFLATI, permessi la reazione regioselettiva del gruppo idrossile 5′ permettersi i nucleosidi disaccaride. Questo metodo potrebbe essere applicato a vari nucleosidi, quali guanosina, adenosina, citidina, uridina, 5-metyluridine e 5-fluorouridine. In questo articolo e il video di accompagnamento rappresentano informazioni utili (visivo) per la O– glicosilazione dei nucleosidi non protetti e loro analoghi per la sintesi di non solo nucleosidi disaccaride, ma anche una varietà di biologicamente rilevanti derivati.

Introduction

Nucleosidi disaccaride, che sono coniugati di un nucleoside e una parte del carboidrato collegato tramite un O-glicosidici bond, costituiscono un’importante classe di naturale carboidrati derivati¹^,² ^,³^,⁴^,⁵^,⁶^,⁷. Per esempio, sono incorporati in macromolecole biologiche quali tRNA (acido ribonucleico transfer) e poli (ADP = adenosina difosfato), così come in alcuni agenti antibatterici e altre sostanze biologicamente attive (ad es., adenophostins, amicetins, ezomycin)⁵^,⁶^,⁸^,⁹^,¹⁰^,¹¹^,¹²^,¹³^, ¹⁴^,¹⁵^,¹⁶^,¹⁷^,¹⁸^,¹⁹. Quindi, disaccaride nucleosidi e loro derivati devono essere composti di piombo per la ricerca di scoperta di farmaci. Le metodologie per la sintesi dei nucleosidi disaccaride sono classificate in tre categorie; enzimatica O– glicosilazione²⁰^,²¹, chimico N– glicosilazione⁵^,⁹^,¹⁶^,²²^,²³^, ²⁴e chimici O– glicosilazione⁷^,⁹^,¹⁴^,¹⁶^,¹⁸^,¹⁹^,²⁴^, ²⁵^,²⁶^,²⁷^,²⁸^,²⁹^,³⁰^,³¹^,³²^,³³^, ³⁴^,³⁵^,³⁶^,³⁷. In particolare, chimica O– glycosylation sarebbe un metodo efficiente per la sintesi stereoselettiva e sintesi su larga scala dei nucleosidi disaccaride. Precedenti ricerche hanno dimostrato che l’O– glycosylation di 2′-trifosfati 2 con il thioglycosyl donatore 1, utilizzando la combinazione di p– toluenesulfenyl cloruro e argento triflato, garantisce la desiderato disaccaride nucleosidici 3 (Figura 1A; AR = arilico e PG = protezione gruppo)³⁸.

A seguito di questi risultati, abbiamo deciso di sviluppare il O– glycosylation di applicazione del sistema di promotore triflato argento/cloruro di p– toluenesulfenyl ribonucleosides. Mentre diversi esempi di O– glicosilazione di ribonucleosides parzialmente protette sono state dimostrate⁷^,⁹^,¹⁴^,¹⁶^,¹⁸^,¹⁹ ^,²⁴^,³²^,³³^,³⁴^,³⁵^,³⁶^,³⁷, l’uso di non protetto o protetto da temporaneamente ribonucleosides come un accettore di glicosil per O– glycosylation è stata segnalata in modo trascurabile. Di conseguenza, lo sviluppo di regioselettiva O– glicosilazione di ribonucleosides temporaneamente protetto o non protetto sarebbe fornire un metodo sintetico più vantaggioso senza proteggere le manipolazioni di gruppo di ribonucleosides. Al fine di raggiungere la regioselettiva O– glicosilazione di ribonucleosides, ci siamo concentrati sui composti del boro, perché diversi esempi di acilazione di regio – e/o stereoselettiva, alchilazione, sililazione e glicosilazione del carboidrato strumenti derivati assistiti da boronico o acido Borinici sono stati segnalati³⁹^,⁴⁰^,⁴¹^,⁴²^,⁴³^,⁴⁴^,⁴⁵ ^,⁴⁶^,⁴⁷^,⁴⁸^,⁴⁹^,⁵⁰. In questo articolo, dimostriamo la procedura per la sintesi dei nucleosidi disaccaride che utilizzano regioselettiva O– glicosilazione presso il gruppo di 5′-idrossile di ribonucleosides via boronico intermedio. Nella strategia presentata qui, estere boronico intermedio 6 sarebbe essere garantita da esterificazione del ribonucleoside 4 con la boronico acido 5, che permette la regioselettiva O– glicosilazione presso il gruppo di 5′-idrossile con thioglycosyl donatore 7 per dare il disaccaride nucleosidici 8 (Figura 1B)⁵¹. Inoltre abbiamo studiato l’interazione di un ribonucleoside e Acido boronico dalla spettroscopia di risonanza magnetica nucleare (NMR), per osservare la formazione di un estere boronico. Esterificazione per rendere boronico e una reazione di glicosilazione richiedono condizioni anidra per evitare l’idrolisi dell’estere boronico e glicosil donatore. In questo articolo, dimostriamo le tipiche procedure per ottenere le condizioni anidra per reazioni di glicosilazione successo per ricercatori e studenti non solo in chimica, ma anche in altri campi di ricerca.

Protocol

Nota: Tutti i dati sperimentali [NMR, spettroscopia infrarossa (IR), spettroscopie di massa (MS), ottiche rotazioni e dati di analisi elementale] dei composti sintetizzati sono stati segnalati in un precedente carta51. 1. procedura di O- glicosilazione reazioni Sintesi di composti α/β-12 (12 di voce nella tabella 1)Nota: 1-13 di voci nella tabella 1 sono state effettuate utilizzando una procedura simile. <li…

Representative Results

I risultati di O- glicosilazione di uridina 10 con thiomannoside α -9 sono riassunti in tabella 160,61. Nella voce 1, O- glycosylation di 10 con α -9 in assenza di derivati dell’acido Boronici ha provocato la formazione di una miscela complicata. Nella voce 2, 10 e phenylboronic acido 11a erano…

Discussion

Lo scopo di questo manoscritto è quello di mostrare un metodo sintetico conveniente per preparare nucleosidi disaccaride utilizzando ribonucleosides non protetti senza manipolazioni di gruppo protezione noioso. Segnaliamo qui il regioselettiva O– glycosylations di nucleosidi tramite il temporaneo 2′, 3′-diolo protezione da un estere boronico ciclico (Figura 1B)⁵¹.

La preparazione dell’estere boronico cicl…

Açıklamalar

The authors have nothing to disclose.

Acknowledgements

Questa ricerca è stata finanziata da donazioni dal Ministero della pubblica istruzione, cultura, sport, scienza e tecnologia (MEXT) del Giappone (nn. 15 00408 K, 24659011, 24640156, 245900425 e 22390005 per Shin Aoki), da una sovvenzione della ricerca biochimica di Tokyo Foundation, Tokyo, Giappone e dal fondo per le aree di ricerca strategica TUS (Tokyo University of Science). Vorremmo ringraziare Noriko Sawabe (facoltà di scienze farmaceutiche, Università delle scienze di Tokyo) per le misurazioni degli spettri NMR, Fukiko Hasegawa (facoltà di scienze farmaceutiche, Università delle scienze di Tokyo) per le misurazioni della massa spettri e Tomoko Matsuo (Istituto di ricerca per la scienza e tecnologia, Tokyo University of Science) per le misurazioni delle analisi elementare.

Materials

Silver trifluoromethanesulfonate	Nacalai Tesque	34945-61
Phenylboronic acid (contains varying amounts of anhydride)	Tokyo Chemical Industry	B0857
p-Methoxyphenylboronic acid	Wako Pure Chemical Industries	321-69201
4-(Trifluoromethyl)phenylboronic acid (contains varying amounts of anhydride)	Tokyo Chemical Industry	T1788
2,4-Difluorophenylboronic acid (contains varying amounts of anhydride)	Tokyo Chemical Industry	D3391
Cyclopentylboronic acid (contains varying amounts of Anhydride)	Tokyo Chemical Industry	C2442
4-Nitrophenylboronic acid (contains varying amounts of anhydride)	Tokyo Chemical Industry	N0812
4-Hexylphenylboronic acid (contains varying amounts of anhydride)	Tokyo Chemical Industry	H1489
Adenosine	Merck KGaA	862.
Guanosine	Acros Organics	411130050
Cytidine	Tokyo Chemical Industry	C0522
Uridine	Tokyo Chemical Industry	U0020
5-Fluorouridine	Tokyo Chemical Industry	F0636
5-Methyluridine	Sigma	M-9885
Methylamine (40% in Methanol, ca. 9.8mol/L)	Tokyo Chemical Industry	M1016
N,N-dimethyl-4-aminopyridine	Wako Pure Chemical Industries	044-19211
Acetic anhydride	Nacalai Tesque	00226-15
Pyridine, Dehydrated	Wako Pure Chemical Industries	161-18453
Acetonitrile	Kanto Chemical	01031-96
1,4-Dioxane	Nacalai Tesque	13622-73
Dichloromethane	Wako Pure Chemical Industries	130-02457
Propionitrile	Wako Pure Chemical Industries	164-04756
Molecular sieves 4A powder	Nacalai Tesque	04168-65
Molecular sieves 3A powder	Nacalai Tesque	04176-55
Celite 545RVS	Nacalai Tesque	08034-85
Acetonitrile-D3 (D,99.8%)	Cambridge Isotope Laboratories	DLM-21-10
Trifluoroacetic acid	Nacalai Tesque	34831-25
TLC Silica gel 60 F₂₅₄	Merck KGaA	1.05715.0001
Chromatorex	Fuji Silysia Chemical	FL100D
Sodium hydrogen carbonate	Wako Pure Chemical Industries	191-01305
Hydrochloric acid	Wako Pure Chemical Industries	080-01061
Sodium sulfate	Nacalai Tesque	31915-96
Chloroform	Kanto Chemical	07278-81
Sodium chloride	Wako Pure Chemical Industries	194-01677
Methanol	Nacalai Tesque	21914-74
JEOL Always 300	JEOL		Measurement of NMR
Lamda 400	JEOL		Measurement of NMR
PerkinElmer Spectrum 100 FT-IR Spectrometer	Perkin Elmer		Measurement of IR
JEOL JMS-700	JEOL		Measurement of MS
PerkinElmer CHN 2400 analyzer	Perkin Elmer		Measurement of elemental analysis
JASCO P-1030 digital polarimeter	JASCO		Measurement of optical rotation
JASCO PU-2089 Plus intelligent HPLC pump	JASCO		For HPLC
Jasco UV-2075 Plus Intelligent UV/Vis Detector	JASCO		For HPLC
Rheodyne Model 7125 Injector	Sigma-Aldrich	58826	For HPLC
Chromatopac C-R8A	Shimadzu		For HPLC
Senshu Pak Pegasil ODS	Senshu Scientific		For HPLC
p-Toluenesulfenyl chloride			Prepared Ref. 38
Phenyl 6-O-acetyl-2,3,4-tri-O-benzyl-1-thio-a-D-mannopyranoside (a-9)			Prepared Ref. 52
4-Metylphenyl 2,3,4,6-tetra-O-benzoyl-1-thio-b-D-galactopyranoside (b-21)			Prepared Ref. 53
4-Metylphenyl 2,3,4,6-tetra-O-benzoyl-1-thio-b-D-glucopyranoside (b-31)			Prepared Ref. 57
4-Metylphenyl 2,3,4,6-tetra-O-benzoyl-1-thio-a-D-Mannopyranoside (a-32)			Prepared Ref. 67
6-N-Benzoyladenosine (14)			Prepared Ref. 54
2-N-Isobutyrylguanosine (16)			Prepared Ref. 55
4-N-Benzoylcytidine (20)			Prepared Ref. 56

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Regioselective O-glycosylation Nucleoside Boronic Ester Disaccharide Nucleoside Temporary Diol Protection Drug Discovery Glycosylation Unprotected Nucleoside Reaction Optimization Synthesis

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Someya, H., Itoh, T., Kato, M., Aoki, S. Regioselective O-Glycosylation of Nucleosides via the Temporary 2′,3′-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides. J. Vis. Exp. (137), e57897, doi:10.3791/57897 (2018).